Triethylamine → HCID 136401067, compound

HRID 2297096Notes

Reaction equation

HRID 2297096 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([NH:21][CH2:22][C@H:23]([NH:28][S:29]([C:32]4[C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[CH:35]=[CH:34][CH:33]=4)(=[O:31])=[O:30])[C:24]([O:26]C)=[O:25])=[O:20])=[CH:16][CH:17]=3)[CH:12]=[N:11]2)[N:3]=1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([NH:21][CH2:22][C@H:23]([NH:28][S:29]([C:32]4[C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[CH:35]=[CH:34][CH:33]=4)(=[O:30])=[O:31])[C:24]([OH:26])=[O:25])=[O:20])=[CH:16][CH:17]=3)[CH:12]=[N:11]2)[N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 136401068HCID 136401068, compound

Product 1

HCID 136401067HCID 136401067, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-[1-[2-amino-4-oxopyrimidin-6-ylmethyl]-indazol-5-yl-carbonylamino]-2(S) -(1-naphthalenesulfonylamino)propionate. A mixture of the product prepared according to Example E-24 Part F (85 mg, 298 μmol) and the product prepared according to Example E-24 Part H (113 mg, 328 μmol) in N,N-dimethylformamide (3 mL) was treated sequentially with triethylamine (52 μL, 373 μmol), 1-hydroxybenzotriazole hydrate (40 mg, 298 μmol) and dicyclohexylcarbodiimide (68 mg, 328 μmol). The mixture was stirred at room temperature for 24 h and concentrated. The residue was purified by flash chromatography (dichloromethane-methanol, 97:3 then 9:1) to provide the title product (154 mg, 89%) as a gum: 1H NMR (MeOH-d4) d 8.64 (d, 1H), 8.15 (s, 2H), 7.92 (d, 1H), 7.89 (s, 1H), 7.71 (d, 1H), 7.6-7.3 (4H), 5.35 (s, 2H), 5.03 (s, 1H), 4.20 (dd, 1H), 3.64 (dd, 1H), 3.46 (dd, 1H); ester methyl signal obscured by residual MeOH signal.

Workup

  1. additionA mixture of the product
  2. customprepared
  3. customthe product prepared
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (dichloromethane-methanol, 97:3

Sources & evidence

ORD record
ord-030d379f7a2944898c649c7b149a93ca
Source dataset
uspto-grants-2002_12
Patent number
US06489333B2

Reaction notes

Loading…